trisodium octahydrate [(2R,3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]methyl hydrogen phosphate

• ChemBase ID: 156018
• Molecular Formular: C6H27Na3O20P2
• Molecular Mass: 550.183412
• Monoisotopic Mass: 550.02639937
• SMILES: C([C@@H]1[C@H]([C@@H]([C@](O1)(COP(=O)(O)[O-])O)O)O)OP(=O)([O-])[O-].O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)([O-])[O-])O[C@]([C@H]1O)(O)COP(=O)(O)[O-].O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C6H14O12P2.3Na.8H2O/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15;;;;;;;;;;;/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15);;;;8*1H2/q;3*+1;;;;;;;;/p-3/t3-,4-,5+,6-;;;;;;;;;;;/m1.........../s1
• InChIKey: DBTJWGHAMYSWQR-MNDNZJPOSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium octahydrate [(2R,3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]methyl hydrogen phosphate
• IUPAC Traditional name: trisodium octahydrate [(2R,3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]methyl hydrogen phosphate
• Synonyms: D-Fructose 1,6-diphosphate trisodium salt; FDP-Na3H; D-Fructose 1,6-bisphosphate trisodium salt octahydrate

Database IDs

• CAS Number: 81028-91-3
• EC Number: 253-778-0
• MDL Number: MFCD00149340
• Beilstein Number: 3837985
• PubChem SID: 162250156; 24871455
• PubChem CID: 16213208

CALCULATED PROPERTIES

• Acid pKa: 0.8894222
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -7.8993273
• LogD (pH = 7.4): -10.122648
• Log P: -3.0051315
• Molar Refractivity: 54.7415 cm^3
• Polarizability: 24.107378 Å^3
• Polar Surface Area: 211.93 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (NT)
• Impurities: ~25% water
• Empirical Formula (Hill Notation): C6H11Na3O12P2 · 8H2O

DETAILS

Sigma Aldrich - 47810

Application
D-Fructose-1,6-bisphosphate (FBP), a common metabolic sugar, is the precursor of glyceraldehyde 3-phosphate and dihydroxyacetone phosphate in the glycolytic pathway. It is an allosteric activator of enzymes such as pyruvate kinase and a substrate used to identify and characterize enzymes such as fructose-1,6-bisphosphate aldolase(s) and fructose-1, 6-bisphosphatase(s). FBP is studied as a neuroprotective agent in brain injury.